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Öğe Azo-azomethine based palladium(II) complexes as catalysts for the Suzuki-Miyaura cross-coupling reaction(Elsevier, 2020) Sunbul, Ali Burak; Inan, Ayse; Kose, Muhammet; Evren, Enes; Gurbuz, Nevin; Ozdemir, Ismail; Ikiz, MesutSeven azo-azomethine ligands (2-8) have been synthesized from the reaction of (E)-5-((4-chlorophenyl) diazenyl)-2-hydroxybenzaldehyde with different aniline derivatives. Ligand structures were characterized by the combination of IR, UVeVisible spectroscopy, C-13 NMR, H-1 NMR and elemental analyses. The mononuclear Pd(II) complexes of these azo-azomethine compounds were prepared with sodium tetrachloropalladate(II) and characterized. According to the UVevisible, FTIR, elemental analyze and HRMS data, the Pd (II) complexes 9-15 are formed by the coordination of N, O atoms of the ligands. Solid state structures of 2, 6 and 7 were determined by single crystal X-ray diffraction studies. Also, Pd(II) complexes were used catalysts for Suzuki-Miyaura coupling reactions of phenylboronic acid with aryl bromide in aqueous media. When the catalytic studies were evaluated, it was found that all of the complexes were suitable for the Suzuki-Miyaura cross-coupling reaction. (c) 2020 Elsevier B.V. All rights reserved.Öğe Heteroaromatik bileşiklerin arilasyonu(İnönü Üniversitesi, 2019) Evren, EnesEkonomik açıdan önemli sayılabilecek birçok farmasötik veya zirai kimyasal madde, vazgeçilemez alt yapılar olarak heteroaril birime sahip olduğundan, heteroaromatik bileşikler, biyoloji veya malzeme bilimleri gibi çeşitli alanlarda çok çeşitli uygulamaları içeren kapsamlı bir geçmişe sahip önemli yapısal birimlerdir. Heteroarenlerin aril halojenürlerle doğrudan arillenmesi modern organik sentezde C-C bağlarının oluşumu için en değerli yöntem haline gelmiştir. Aril halojenürler ve heteroarenler arasındaki doğrudan eşleşme, tepkime aşamalarının en aza indirilmesi ve yan ürün oluşumunun azaltılması açısından avantajlıdır. Son yıllarda, bu alandaki çok çeşitli çalışmalar yeni C-H bağ dönüşümlerinin gelişimine odaklanmıştır. Bu gelişmeden sonra, piroller, azoller, (benzo) tiyofenler ve (benzo) furanlar gibi diğer değerli heteroarenlerin doğrudan arillenmesi için çeşitli yöntemler geliştirilmiştir. N-heterosiklik karben (NHC) ligandları, elektronik ve sterik olarak kontrol edilebilir ve genellikle farklı metal iyonları ile termal olarak kararlı bileşikler oluştururlar. NHC ligandlarının güçlü σ-donör fakat zayıf π-alıcı özellikleri, birçok kararlı palladyum(II)-NHC kompleksinin oluşumunu da sağlamaktadır. Palladyum(II)-NHC kompleksleri aktivitesi, kararlılığı ve seçiciliği nedeniyle, çok sayıda doğrudan arilleme reaksiyonunda oldukça reaktif ve seçici katalizörler olarak yaygın şekilde kullanılmıştır. Bu amaçla tez kapsamında yeni karben öncülleri ve palladyum kompleksleri sentezlenerek heteroaromatik bileşiklerin arilasyonu tepkimelerindeki katalitik aktiviteleri incelenmiştir. Elde edilen bulgular üç alt basamakta toplanabilir: 1) Alkil halojenürler ile 1-(2-Etilhekzilbenzimidazol) kullanılarak benzimidazolyum tuzları (1a-1k) sentezlendi ve yapıları uygun spektroskopik yöntemler ile açıklandı. 2) Sentezlenen benzimidazolyum tuzları, PdCl2 ve Pd(OAc)2 ile uygun şartlarda etkileştirilerek Pd-NHC Kompleksleri sentezlendi ve yapıları aydınlatıldı (2a-2h ve 3a-3c) 3) Sentezlenen Pd-NHC komplekslerinin heteroaromatik bileşiklerin arilasyon tepkimesindeki katalitik aktiviteleri incelendi.Öğe Plausible PEPPSI catalysts for direct C-H functionalization of furans and pyrroles(Elsevier, 2024) Munir, Naima; Gurbuz, Navin; Zafar, M. Naveed; Evren, Enes; Sen, Betul; Aygun, Muhittin; Ozdemir, IsmailThe worth of bi(hetero)arenes in ongoing medicinal and industrial research fields promotes their efficient synthesis by Pd-PEPPSI-bearing NHC spectator ligands encapsulated as site-selective direct C-H functionalization agents. Eight new asymmetric N-heterocyclic carbenes ligands and their plausible pyridine-assisted Pd (II) complexes are reported in this work. The synthesized compounds were thoroughly characterized by respective spectroscopic techniques, such as 1H, 13C, FTIR and elemental analysis. The structures of synthesized pro-ligand salts and complexes were determined by Single Crystal XRD. The on/off mechanism of pyridine assisted Pd-NHC complexes made them the best C-H functionalized catalysts for regioselective C5 arylated products. Five membered heterocyclic compounds such as 2-acetyl furan, furfuryl acetate and 1-methyl-2-pyrrole-carboxylaldehyde were treated with numerous aryl bromides under optimal catalytic reaction conditions. Furfuryl acetate was used for the first time as a substrate in the present research work. Interestingly, all the prepared catalysts possessed essential structural features that facilitated the formation of desired coupled products in quantitative yield with excellent selectivity.Öğe Rhodium(i) N-heterocyclic carbene complexes: synthesis and cytotoxic properties(Royal Soc Chemistry, 2021) Slimani, Ichraf; Sahin-Bolukbasi, Serap; Ulu, Mustafa; Evren, Enes; Gurbuz, Nevin; Ozdemir, Ilknur; Hamdi, NaceurRhodium(i) complexes bearing N-heterocyclic carbene (NHC) ligands have been widely used in catalytic chemistry, but there are very few reports of biological properties of these types of complexes. A series of benzimidazolium salts and their [RhCl(NHC)(COD)] complexes were synthesized. The obtained complexes were synthesized and characterized by elemental analysis, FT-IR, H-1 and C-13 NMR. All compounds were screened for in vitro cytotoxic activities against a panel of human cancer cells (HT-29 colon, Ishikawa endometrial, and U-87 glioblastoma) using the MTT assay for 48 h of incubation time. Mouse fibroblast cells (L-929) were used as healthy cells. Complexes had exhibited significantly higher cytotoxic activity towards cancer cells than their ligands and complex 2b showed the most selective cytotoxic activity against HT-29 cancer cells (SI;7.05) and Ishikawa cancer cells (SI; more than 9.8). The complexes showed strong in vitro cytotoxic activity against cancer cells, with IC50 values of lower than 10 mu M (except 2a against HT-29 (12.8 mu M) and 2b against U-87 (11.1 mu M)). All complexes (2a-d) showed the highest in vitro cytotoxic activity against Ishikawa endometrial cancer cells with IC50 values of 2.93 +/- 0.06, <1, 2.60 +/- 0.05, and 2.85 +/- 0.06 mu M, respectively. Complexes were found to be highly cytotoxic against HT-29, Ishikawa, and U-87 cancer cells compared to the anticancer agents, cisplatin and 5-FU.Öğe Ruthenium(II) complexes bearing N-heterocyclic carbene ligands with wingtip groups and their catalytic activity in the transfer hydrogenation of ketones(Elsevier Science Sa, 2020) Yigit, Beyhan; Isik, Yilmaz; Celepci, Duygu Barut; Evren, Enes; Yigit, Murat; Gurbuz, Nevin; Ozdemir, IsmailA series of new silver(I) complexes bearing N-heterocyclic carbene (NHC) ligands with wingtip groups were synthesized by the reaction of 1,3-dialkylimidazolinium salts with silver(I) oxide in dichloromethane. The silver complexes were used as carbene-transfer agents to synthesize ruthenium(II) complexes with the general formula [RuCl2(NHC)(eta(6)-p-cymene)]. All the synthesized complexes were characterized by elemental analysis, FT-IR, H-1 NMR and C-13 NMR spectroscopy, and the molecular and crystal structure of 3d was determined by single-crystal X-ray diffraction. These ruthenium complexes were tested as catalysts in the transfer hydrogenation of ketones using (PrOH)-Pr-i as a hydrogen source. All compounds tested showed good catalytic activity in these reactions.Öğe Synthesis and in silico studies of Novel Ru(II) complexes of Schiff base derivatives of 3-[(4-amino-5-thioxo-1,2,4-triazole-3-yl)methyl]-2(3H)-benzoxazolone compounds as potent Glutathione S-transferase and Cholinesterases Inhibitor(Elsevier, 2021) Adiguzel, Ragip; Turkan, Fikret; Yildiko, Umit; Aras, Abdulmelik; Evren, Enes; Onkol, TijenNovel Ru(II) complexes of Shiff base derivatives of 3-[(4-amino-5-thioxo-1,2,4-triazole-3-yl)methyl]-2(3H)benzoxazolone were synthesized. The ligands (1a-e) were confirmed by IR, H-1 NMR, and C-13 NMR spectra (only 1b and 1c). Structures of the synthesized Ru(II) complexes (2a-e) were illuminated by elemental analysis, IR, H-1 NMR, C-13 NMR, and mass spectra. As the biological studies, the inhibitory potency of the ligands and the novel synthesized complexes were evaluated against the glutathione S-transferase (GST), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes in vitro conditions. Ki values in the range of 26.87-47.63 mu M for AChE, 23.51-42.81 mu M for BChE, and 33.14-51.73 mu M for GST, respectively. The free binding energy of most active inhibitors against AChE, BChE, and GST enzymes were detected as-10.183 kcal/mol, -9.111 kcal/mol, and -6.097 kcal/mol, respectively. All compounds docked were observed to bind in the active site of the enzymes with similar binding orientation and binding interactions with the surrounding amino acids. (C) 2021 Published by Elsevier B.V.Öğe Synthesis, characterization and antitumor properties of novel silver(I) and gold(I) N-heterocyclic carbene complexes(Elsevier Science Sa, 2020) Ozdemir, Ilknur; Ciftci, Osman; Evren, Enes; Gurbuz, Nevin; Kaloglu, Nazan; Turkmen, Nese Basak; Yasar, SeymaIn this study, two novel benzimidazolium salts consisting propane sulfonate order were integrated in high yields as N-heterocyclic carbene (NHC) precursors. The silver-NHC buildings were set up by responding 1-(2,2-dimethoxyahyl)-3-(propyl-3-sulfonate)benzimidazolium and 1-(2,2-diethoxyahyl)-3-(propyl-3-sulfonate)benzimidazolium with silver oxide on average state. Gold-NHC edifices were acquired by means of transmetallation of their silver precursors with [AuCl{S(CH3)(2)}]. The structures of all mixes were completely portrayed by spectroscopic techniques H-1 NMR, C-13{1H} NMR, IR and elemental and further analyzed by DFT/TDDFT strategies. IC50 values and cytotoxic impacts of these four complexes were controlled by the MTS put together examine with respect to three human cancer cell lines neuroblastoma (SHSY5Y), adenocarcinoma (HEP3B), and human fibroblasts (HF).Öğe Synthesis, structures and catalytic activity of Pd(II) saccharinate complexes with monophosphines in direct arylation of five-membered heteroarenes with aryl bromides(Elsevier Science Sa, 2020) Yilmaz, Veysel T.; Icsel, Ceyda; Turgut, Omer R.; Aygun, Muhittin; Evren, Enes; Ozdemir, IsmailA number of new Pd(II) saccharinate (sac) complexes bearing a range of phenyl (Ph), cyclohexyl (Cy) and alkyl (Me and Et) substituted tertiary phosphine ligands with systematically changing electronic and steric properties, namely trans-[PdCl(sac)(L)(2)] (L = PPh3 (1); PPh2Cy (3)), trans-[Pd(sac)(2)(H2O)(L)] (L = PPh3 (2); PPh2Cy (5)), trans-[Pd(sac)(2)(L)(2)] (L = PPh2Cy (4); PPhCy2 (6); PCy3 (8)), [PdCl(sac)(PCy3)(DMSO)] (7), trans-[Pd (sac)(2)(PPh2Me)(DMSO)] (9) and cis-[M(sac)(2)(L)(2)] (L= PPhMe2 (10); PPh2Et (11); PPhEt2 (12)), were synthesized and structurally characterized. The Pd(II) complexes were applied for direct C2/C5 arylation of fivemembered heteroarenes such as furan, thiophene and thiazole derivatives with aryl bromides. Notably, arylation products up to 99% yields were obtained in the presence of the Pd(II) complexes. The catalytic mechanism of the direct arylation was proposed to proceed via a Pd(0)/Pd(II) pathway, due to elimination of the sac ligand in the Pd(II) complexes during catalysis.
